Organocascade Synthesis of Bicyclo[3.3.1]nonan-9-ones Initiated by an Unusual 1,6-Addition of Cyclohexanones to (E)-2-(3-Arylallylidene)-1H-indene-1,3(2H)-diones

De Chih Wang, Pin Han Huang, Wan Wun Huang, You Song Cheng, Kwunmin Chen

研究成果: 雜誌貢獻文章

2 引文 斯高帕斯(Scopus)

摘要

An efficient organocatalytic cascade reaction for the synthesis of the bicyclo[3.3.1]nonan-9-one skeleton is reported. The cascade reaction proceeds smoothly between prochiral 4-substituted cyclohexanones and (E)-2-(3-arylallylidene)-indene-1,3-diones involving a 1,6-/γ-protonation/1,4-addition sequence to construct bicyclic products that contain five stereogenic centers in good to high chemical yields and excellent diastereo- and enantioselectivity (up to >20:1 dr and 97% ee) in the presence of a thioether-linked l-prolinol-camphor-derived organocatalyst at ambient temperature. An interesting organocatalytic three-component triple cascade reaction has been performed to produce a bicyclo[2.2.2]octan-2-one in a favorable chemical yield and stereoselectivity (>19:1 dr and 97% ee) starting from 1,3-indanedione, an enal, and cyclohexenone in the presence of a primary amine organocatalyst. (Figure presented.).

原文英語
頁(從 - 到)3005-3013
頁數9
期刊Advanced Synthesis and Catalysis
359
發行號17
DOIs
出版狀態已發佈 - 2017 九月 4

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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